Soleymani Elham, Alinezhad Heshmatollah, Darvish Ganji Masoud, Tajbakhsh Mahmood
Department of Organic Chemistry, Faculty of Chemistry, University of Mazandran, Babolsar, Iran.
J Mater Chem B. 2017 Sep 7;5(33):6920-6929. doi: 10.1039/c7tb00755h. Epub 2017 Aug 9.
The enantioseparation of chiral drugs has been of great interest in the modern pharmaceutical industry since the majority of bioorganic compounds are chiral. In this work, we have investigated the ability of pristine and defected (10, 5) chiral carbon nanotubes (CNTs) in enantioseparation of chiral R-/S-ibuprofen isomers. The interactions between the two enantiomers of ibuprofen and the outer surface and inner side wall of the chiral CNTs have been evaluated. We utilized dispersion-corrected density functional theory (DFT) calculations within the framework of the GGA-PBE scheme for the systems under study. The results indicated that the inner side walls of the defected (10, 5) CNTs exhibited the highest energy difference (ΔU) between the pairs of considered enantiomers with the energy difference of about 1.4 kcal mol, indicating that these nanotubes are a promising candidate in enantioseparation processes. The effect of solvation has also been considered in the calculations and it was found that changing the dielectric properties of the medium cannot affect the overall interactions between the drug and CNT. The electronic properties of the considered systems did not change upon the interaction between the incorporated molecules and the type of interaction was found to be dispersion-governed physisorption.
由于大多数生物有机化合物都是手性的，手性药物的对映体分离在现代制药工业中备受关注。在这项工作中，我们研究了原始的和有缺陷的(10, 5)手性碳纳米管(CNT)对对映体R-/S-布洛芬异构体的对映体分离能力。评估了布洛芬两种对映体与手性碳纳米管外表面和内侧壁之间的相互作用。我们在所研究的体系框架内，利用GGA-PBE方案下的色散校正密度泛函理论(DFT)计算。结果表明，有缺陷的(10, 5)碳纳米管的内侧壁在所考虑的对映体对之间表现出最高的能量差(ΔU)，能量差约为1.4 kcal mol，表明这些纳米管是对映体分离过程中有前景的候选材料。计算中还考虑了溶剂化的影响，发现改变介质的介电性质不会影响药物与碳纳米管之间的整体相互作用。所考虑体系的电子性质在掺入分子之间的相互作用后没有改变，并且发现相互作用类型是色散主导的物理吸附。
